Advanced Catalysts for Olefin Synthesis: Copper(II) Quinoline-Fused Oxazolidines in Alcohol Dehydration

The new copper(II) catalyst [Cu(<sup>Q</sup>FOX)(CH<sub>3</sub>CN)][OTf]<sub>2</sub> has been synthesized and found to be active for alcohol dehydration to give olefins at 120 °C with a 1% catalyst loading (<sup>Q</sup>FOX = di-2-quinolinyl-fused-oxazolidine). Benzylic, allylic, and tertiary alcohols are all dehydrated. In some cases, ethers are observed to be produced, but these are re-entrained into the catalytic cycle. Unactivated secondary alcohols are also dehydrated. Similar catalysts employing Mn<sup>II</sup>, Fe<sup>II</sup>, Co<sup>II</sup>, and Ni<sup>II</sup> were also synthesized but showed reduced dehydration activity compared to the copper(II) derivative. A Cu<sup>I</sup> analog was also prepared but did not show improved dehydration activity.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-12-31
DOI
https://doi.org/10.1021/acs.joc.5c02669
Primary Topic
Carbon dioxide utilization in catalysis
Type
article
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article

Advanced Catalysts for Olefin Synthesis: Copper(II) Quinoline-Fused Oxazolidines in Alcohol Dehydration

Ameesh Panda, William D. Jones, William W. Brennessel, Ruilin Zhang
The Journal of Organic Chemistry
Carbon dioxide utilization in catalysis
article

Advanced Catalysts for Olefin Synthesis: Copper(II) Quinoline-Fused Oxazolidines in Alcohol Dehydration

Ameesh Panda, William D. Jones, William W. Brennessel, Ruilin Zhang
article en

Abstract

The new copper(II) catalyst [Cu(<sup>Q</sup>FOX)(CH<sub>3</sub>CN)][OTf]<sub>2</sub> has been synthesized and found to be active for alcohol dehydration to give olefins at 120 °C with a 1% catalyst loading (<sup>Q</sup>FOX = di-2-quinolinyl-fused-oxazolidine). Benzylic, allylic, and tertiary alcohols are all dehydrated. In some cases, ethers are observed to be produced, but these are re-entrained into the catalytic cycle. Unactivated secondary alcohols are also dehydrated. Similar catalysts employing Mn<sup>II</sup>, Fe<sup>II</sup>, Co<sup>II</sup>, and Ni<sup>II</sup> were also synthesized but showed reduced dehydration activity compared to the copper(II) derivative. A Cu<sup>I</sup> analog was also prepared but did not show improved dehydration activity.

The Journal of Organic ChemistryVol. 91(2)
University of Rochester (US)
Clean water and sanitation
Openalex Percentile: Top 45%
Carbon dioxide utilization in catalysis
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